Enfuvirtide

Summary

Enfuvirtide (CHEMBL525076) is an approved protein HIV fusion inhibitor (ATC J05AX07); indicated across 4 conditions including viral infectious disease and hiv infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Protein
• ATC class: J05AX07
• Indications: 4 conditions
• Clinical trials: 36
• Chemistry: 4492 Da · C204H301N51O64

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL525076
Name	Enfuvirtide
Type	Protein
Max phase	4
FDA approved	yes
PubChem CID	16130199
ChEBI	CHEBI:608828
ATC	J05AX07
Molecular formula	C204H301N51O64
Molecular weight	4492
InChIKey	PEASPLKKXBYDKL-FXEVSJAOSA-N

SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@@H](CC7=CC=CC=C7)C(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC8=CN=CN8)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC9=CC=C(C=C9)O)NC(=O)C

IUPAC name: (4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-amino-5-oxopentanoyl]amino]-4-amino-4-oxobutanoyl]amino]-5-amino-5-oxopentanoyl]amino]-5-amino-5-oxopentanoyl]amino]-5-[[(2S)-6-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-oxopentanoic acid

ChEBI definition: A synthetic 36-amino acid peptide consisting of N-acetyltyrosyl, threonyl, seryl, leucyl, isoleucyl, histidyl, seryl, leucyl, isoleucyl, α-glutamyl, α-glutamyl, seryl, glutaminyl, asparaginyl, glutaminyl, glutaminyl, α-glutamyl, lysyl, asparaginyl, α-glutamyl, α-glutamyl, α-glutamyl, leucyl, leucyl, α-glutamyl, leucyl, α-aspartyl, lysyl, tryptophyl, alanyl, seryl, leucyl, tryptophyl, asparaginyl, tryptophyl, and phenylalaninamide residues joined in sequence. An HIV fusion inhibitor, it was the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection. It interferes with entry of HIV into cells by binding to the gp41 sub-unit of the viral envelope glycoprotein, so inhibiting fusion of viral and cellular membranes.

Pharmacological roles (ChEBI): HIV fusion inhibitor.

Also known as: DP-178, DP178, Enfuvirtida, Enfuvirtide, Fuzeon, Fuzeon t-20, Pentafuside (trivial name), T-20, T20, YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWF, enfuvirtide, ENFUVIRTIDE

Parent form; salt/anhydrous children: CHEMBL4085102

Patent coverage: 5,022 distinct patent families (19,493 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 19,158 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

No target linkage available.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
viral infectious disease	4	MONDO:0005108	EFO:0000763
HIV infectious disease	4	MONDO:0005109	EFO:0000764

1 disease in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
AIDS	3	MONDO:0012268	EFO:0000765

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 36.

Phase distribution

Phase	Trials
PHASE4	14
PHASE2	8
PHASE3	6
PHASE1	3
Not specified	3
PHASE1/PHASE2	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00100984	PHASE4	TERMINATED	A 48 Week Study Comparing Treatment With Saquinavir + Lopinavir/Ritonavir in Combination With Enfuvirtide HAART Versus Saquinavir + Lopinavir/Ritonavir + Other Nucleoside Combinations to See the Efficacy of These Treatments in Patients Infected With HIV-1
NCT00187551	PHASE4	COMPLETED	Pilot Study Evaluating Interruption of Enfuvirtide (Fuzeon, T20) in Patients With Enfuvirtide Resistance
NCT00192660	PHASE4	COMPLETED	HIV Infection And Metabolic Abnormalities Protocol 1 (HAMA001)
NCT00232908	PHASE4	COMPLETED	QUALITE Study - A Study of Fuzeon (Enfuvirtide) in Treatment-Experienced Patients With Human Immunodeficiency Virus-1 (HIV-1) Infection
NCT00233883	PHASE4	COMPLETED	WAND Study - A Study to Evaluate Fuzeon (Enfuvirtide) Administered by a Needle-Free Injection Device in Patients With HIV.
NCT00326963	PHASE4	COMPLETED	BLQ Study: A Study of a Protease Inhibitor With Fuzeon (Enfuvirtide) in Treatment-Experienced Patients With HIV-1.
NCT00337701	PHASE4	COMPLETED	BOSS Study: A Study of Fuzeon Using the Needle-Free Biojector 2000 in Patients With HIV-1 Infection
NCT00344760	PHASE4	COMPLETED	A Study to Evaluate of the Efficacy of Enfuvirtide During the Induction Phase of Therapy
NCT00461266	PHASE4	WITHDRAWN	ESP Study: A Study to Assess the Effect of Adding Fuzeon (Enfuvirtide) to an Antiretroviral Regimen in Fuzeon-Naive Patients With Sustained HIV Viral Suppression.
NCT00487188	PHASE4	COMPLETED	A Study to Evaluate the Safety and Efficacy of Adding Enfuvirtide to Oral Highly Active Antiretroviral Therapy (HAART) in Human Immunodeficiency Virus (HIV) Patients With Prior Treatment Experience
NCT00488059	PHASE4	TERMINATED	A Study of Fuzeon (Enfuvirtide) With an Integrase Inhibitor Plus Optimized Background in Treatment-Experienced HIV-1 Infected Patients
NCT00657761	PHASE4	COMPLETED	Metabolic Effects of Enfuvirtide in Healthy Volunteers
NCT02569502	PHASE4	COMPLETED	A Study of Enfuvirtide (Fuzeon) in Patients With Advanced Human Immunodeficiency Virus-1 (HIV-1) Infection
NCT02582983	PHASE4	COMPLETED	A Study of Enfuvirtide (Fuzeon) in Participants With Advanced Human Immunodeficiency Virus (HIV) Infection
NCT00008528	PHASE3	COMPLETED	T-20 With Anti-HIV Combination Therapy for Patients With Prior Anti-HIV Drug Treatment and/or Drug Resistance to Each of the Three Classes of Approved Anti-HIV Drugs
NCT00021554	PHASE3	COMPLETED	T-20 in HIV Patients With Prior Drug Treatment and/or Resistance to Each of the Three Classes of Anti-HIV Drugs
NCT00050856	PHASE3	COMPLETED	Fuzeon (Enfuvirtide) Early Access Program for Patients With HIV-1 Infection
NCT00302822	PHASE3	COMPLETED	Intensification With Enfuvirtide in Naive HIV-infected Patients (ANRS130)
NCT00537394	PHASE3	COMPLETED	Optimizing Treatment for Treatment-Experienced, HIV-Infected People
NCT02733419	PHASE3	COMPLETED	Efficacy, and Safety Study of Optimized Background Antiretroviral Regimen (OB) in Combination With Enfuvirtide in the Treatment-Experienced Participants With Human Immunodeficiency Virus-1 (HIV-1) Infection
NCT00002228	PHASE2	COMPLETED	A Study of T-20 in HIV-Positive Adults
NCT00002239	PHASE2	COMPLETED	A Study to Compare Three Doses of T-20 When Given in Combination With Abacavir, Amprenavir, Ritonavir, and Efavirenz to HIV-Infected Adults
NCT00013884	PHASE2	COMPLETED	HIV Maintenance Therapy With T-20 During HAART Interruption
NCT00022763	PHASE2	COMPLETED	T-20 Plus a Selected Anti-HIV Treatment in HIV-Infected Children and Adolescents
NCT00031044	PHASE1/PHASE2	COMPLETED	Adding New Drugs for HIV Infected Patients Failing Current Therapy
NCT00089492	PHASE2	COMPLETED	A Study Comparing the Efficacy and Safety of Once-Daily Fuzeon (Enfuvirtide) Dosing Versus the Currently Recommended Twice-Daily Dosing in Human Immunodeficiency Virus-Type 1 (HIV-1) Infected Patients
NCT00120367	PHASE2	COMPLETED	Early Intensification of Antiretroviral Therapy Including Enfuvirtide in HIV-1-Related Progressive Multifocal Leucoencephalopathy (ANRS125)
NCT00128830	PHASE2	COMPLETED	A Study With TMC125 in Human Immunodeficiency Virus (HIV) Type 1 Infected Patients, Who Were Treated With TMC125 Arm in a Sponsor-Selected TMC125 Study
NCT00615134	PHASE2	COMPLETED	INNOVE Study: A Study of 3 Months Induction With Fuzeon (Enfuvirtide) + Optimized Background (OB) Versus OB Alone in HIV-1 Infected Patients With Virological Failure.
NCT00001118	PHASE1	COMPLETED	Study of a New Anti-HIV Drug, T-20, in HIV-Infected Children
NCT00086710	PHASE1	COMPLETED	Study of Enfuvirtide in HIV-Positive Subjects
NCT00312546	PHASE1	TERMINATED	Study of Valproic Acid to Treat HIV Infected Adults
NCT01836068	EARLY_PHASE1	COMPLETED	Optimized Antiretroviral Therapy During Allogeneic Hematopoietic Stem Cell Transplantation in HIV-1 Individuals
NCT00051831	Not specified	COMPLETED	Effect of an Enfuvirtide-based Anti-HIV Drug Regimen on Latent HIV Reservoirs in Treatment Naive Adults
NCT00216359	Not specified	UNKNOWN	Cohort Study for Patients Using Fuzeon (Enfuvirtide)
NCT00334022	Not specified	COMPLETED	Fuzeon Viral Decay Pilot Study

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).